Cannabis Compound Database: Showing Compound Card for alpha-Gurjunene (CDB000313)

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Record Information

Version

1.0

Created at

2020-03-19 00:30:25 UTC

Updated at

2020-12-07 19:07:21 UTC

CannabisDB ID

CDB000313

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

alpha-Gurjunene

Description

Alpha-Gurjunene or (-)-Alpha-Gurjunene, belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpenoid as it synthesized via isoprene units. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-Gurjunene is a neutral, hydrophobic molecule that is insoluble in water. It exists as a colorless clear liquid and has a woody, balsamic odor. It is used as a perfuming agent. Alpha-gurjunene is found in many plants, essential oils and foods including allspice, bay leaf, carrot seeds, eucalyptus, guava, parsley, black papper, sage and tea tree oil. Alpha-gurjunene is also one of more than 140 terpenes that are found in cannabis plants (PMID: 6991645 ).

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
(-)-a-Gurjunene	Generator
(-)-Α-gurjunene	Generator
a-Gurjunene	Generator
Α-gurjunene	Generator

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.36

Monoisotopic Molecular Weight

204.1878

IUPAC Name

(1aR,4R,4aR,7bS)-1,1,4,7-tetramethyl-1H,1aH,2H,3H,4H,4aH,5H,6H,7bH-cyclopropa[e]azulene

Traditional Name

(-)-α-gurjunene

CAS Registry Number

489-40-7

SMILES

C[C@@H]1CC[C@@H]2[C@H](C3=C(C)CC[C@H]13)C2(C)C

InChI Identifier

InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h9,11-12,14H,5-8H2,1-4H3/t9-,11-,12-,14-/m1/s1

InChI Key

SPCXZDDGSGTVAW-XIDUGBJDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

5,10-cycloaromadendrane sesquiterpenoids

Alternative Parents

Substituents

5,10-cycloaromadendrane sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

carbotricyclic compound (CHEBI:61699 )
sesquiterpene (CHEBI:61699 )

Ontology

Role

Industrial application:

Personal care products:

Perfuming agent

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.45	ALOGPS
logP	4.04	ChemAxon
logS	-4.2	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.5 m³·mol⁻¹	ChemAxon
Polarizability	26.22 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	alpha-Gurjunene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03fr-1900000000-a9f60ba2e6d644daa013	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0290000000-345ad3b09da9e2a50762	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-3970000000-b3966925656c14a82f16	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1170-8900000000-df99e2c36d98b0db95e2	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-1b060cde85b4f43a1531	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0190000000-07f1ef066e7c398c1e83	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-009i-2900000000-67a968fed51e1a89291d	2017-06-28	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-4290000000-9bfe83bd2ec7aa800c45	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-7920000000-b84f94c3b0eeef942277	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-056r-9200000000-079173ace0ae9daa444b	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-10-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0090000000-f72e0de45a6955aeac7c	2021-10-21	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0304686

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15560276

PDB ID

Not Available

ChEBI ID

61699

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]
Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Showing Compound Card for alpha-Gurjunene (CDB000313)

Structure for CDB000313 (alpha-Gurjunene)